Oleic-acid derivative of bodies of the terpene group.



NATHAN SULZBERGER, OF -NEW YORK, N. Y.

OLEIC-AGID DERIVATIVE OF BODIES OF. THE TERIENE GROUP.

No Drawing.

Specification of Letters Patent. A'pplication filed May 6, 1909. Serial No. 494,413.

Patented Sept. 6, 1910.

To all whom it may concern.

Be it known that I, NATHAN SULZBERGER, a citizen of the United States, residing at No. 3 L West Seventy-first street, New York city,'in the county of New York and State of New York, have invented new and useful Products to be Used for Pharmaceutical and Medical Purposes, Oleic-Acid Derivatives of Bodies of the Terpene Group, .of which the following is a specification.

I have found that the oleates of menthol and. other bodies of pharmaceutical value belonging to the terpene group, and their derivatives, while still retaining the soothing and other medical properties of the free uncombined products out of. which they were formed, do not possess the irritating action of the same, and are furthermore characterized by penetrating more rapidly and deeply into the skina fact which markedly improves and increases the value of these oleates, especially when used ex ternally, either by themselves, or in the form of salves and ointments, mixed with animal, vegetable and mineral fats and oils. The oleatescan be prepared by treating the solution of these terpene derivatives, and oleic acid, with dehydrating a ents, as for instance, phosphorus-oxy-ch orid, phosphorus-tri-chlorid, etc., or by bringing the oleic acidichlorid into reaction with these terpene bodies. These new products are almost entirely odorless, and represent oils of a more or less yellowish coloration, insoluble in water and split by the action of caustic soda into the terpene-body, from which they were formed, and sodium oleate.

In order to illustrate my invention more clearly, I shall herewith describe my referred method of preparing the ment olester of oleic acid:

IO ID IS MI' 200 grams of oleic acid (dried) were treated with 42 grams of phosphorus-tri" chlorid, and the mixture, afterstanding for several hours, at ordinary temperature, gradually heated up on the water-bath, to about 80 degrees C. The oleic acid chlorid, freed from the excess of phosphorus tri chlorid, and from the formed phosphorous acid, was brought into reaction with one. molecular proportion (figured on the oleic. acid chlorid) of menthol (dr After the evolutionof hydrochloric aci had ceased at glll? about 80-40 degrees 0., the temperature was gradually raised to about 80-90 degrees (3., and kept there for several hours. The re- -action of the menthol with the oleic-a'cid chlorid takes place according to the following equation o n oooo n noej thol is evinced.

In a similar manner the oleic acid derivativeof borneol can be obtained, namely, by heating a mixture of borneol with an excess of over one molecule of oleic acid chlorid for several hours on a water bath, after such mixture has been standing for some time at ordinary temperature. This borneolpre aration, when'free from the ex'cessof o eic acid chlorid and from the formed phosphorous acid and Washed neutral, is ready for use. In similar manner other alcohols belonging to the terpene group may be heated together with oleic acid, as, for instance, terpineol, iso-borneol, etc.

The above cited examples should only indicate the method of manufacturing and preparing some of the compounds accordto my invention. wish it to be understood that the temperatures and quantities, also the method of purification may be variously changed from the above described.

I claim:

1. The menth l-ester of oleic acid of the nature disclose characterized by being a yellowish oil at ordinary temperature, unsoluble in water, derived from oleic acid and menthol, de-composed by the action of caustic alkali and decolorizing bromin water. I 2. Esters of oleic acid w1th bodies containing an alcoholic hydroxyl belonging to the terpene group of the nature herein disclosed and characterized by being oils of yellowish color at ordinary temperature, un-

soluble in water, decomposed by the actionof caustic alkali, decolorizing bromin water alcohol, de-coloringbromin, and producing and derived by chemically combining oleic sodium-oleate when treated 'With caustic 10 gcid with the lalcoholic hydroxyl of a body soda. 7

e on to t e terpene rou r w 3. gb m pounds derived by eating oleie- NATHAN SULABERGER' acid chlorid and alcohols belonging to the WVitnesses: terpene group, characterized by being oils BENJAMIN SROTER, of a yellowish color, insoluble in Water and JOHN S. COLWELL. 

